


The One

by existential1rony



Category: Chicago PD (TV)
Genre: Developing Relationship, F/M, Light Angst, Partners to Lovers, Romantic Friendship, Slow Burn, So Wrong It's Right
Language: English
Status: In-Progress
Published: 2021-02-23
Updated: 2021-03-09
Packaged: 2021-03-13 06:28:29
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 10,024
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29647167
Author URL: https://archiveofourown.org/users/existential1rony/pseuds/existential1rony
Summary: Hailey and Jay's partnership is nothing short of beautiful. Their bond is strong from early on and there may be more to it than meets the eye. But what happens when the person you're meant to be with is already with someone else? Sometimes you hit a lot of smaller bumps before you can fully get up the mountain.
Relationships: Jay Halstead & Hailey Upton, Jay Halstead/Hailey Upton
Comments: 15
Kudos: 49





	1. Chapter 1

Detective Jay Halstead and Detective Hailey Upton had been partners in Intelligence for over a year now. Despite both of them being in the force for many years combined, it wasn't lost on either of them that they were the best partner the other had ever had. Their first few weeks paired together had been a little rough, mostly in part due to Jay. He wasn't thrilled with getting assigned a female partner. Nothing to do with her gender, of course, but years prior he had dated one of his team members in Organized Crime. And while he thought their relationship had been great, she had been just using him as a stepping stone. The second Narcotics offered her a fat promotion, she walked away from Jay with barely a goodbye. He blamed himself for not seeing the signs, owning it up to being young, a few years removed from the war and just craving a taste of normalcy again. He was well over it now, and he certainly didn't want to judge Hailey based on someone she didn't even know, but still, he was definitely hesitant when their sergeant, Hank Voight paired them up. Add in the fact that Hailey Upton was also a natural looker who didn't even seem to realize it, Jay knew he should keep his distance. Somehow though, she broke down his walls, as he did hers, and soon they had become the best of friends. They both found that they spent more time with each other, between work and having to decompress from work, then they did with almost anyone else.

Which is why it wasn't a shock that Hailey knew Jay was too close to this case, despite him swearing to everyone else he was fine and could handle it. She knew when he was close to spiraling, she always did, she probably knew him better than anyone. The case at hand was trying to solve the arson of an apartment fire that caused the death of five people, including Jay's own father. His dad and him hadn't been close in years, in many ways they never really were. His dad always took to his brother, Will, more. Will was a doctor, spending years studying and applying himself to get out of the Blue-Collar lifestyle that Pat Halstead had worked so hard at so his sons wouldn't have to. So he hated the fact that Jay wasn't studious, hated the fact that Jay had decided to join the army for pennies and risk his life, and then really hated the fact that when his son survived all of that, he chose to become a cop. Add onto the fact that he was a mad-at-the-world Irish drunk who could barely take care of his mother when she was dying from Cancer, Jay hadn't been a fan of his father in a long time. But at the end of the day, your parents were still your parents, we love them in our own ways, and Jay wasn't handling his death anywhere near as well as he thought. Hailey had kept her eyes close on him all week and they had butted heads plenty. She had never been scared to call him out on his shit. She cared, and she was worried.

They had finally found a break in the case. One of the deaths had been Edgar Torres, the leader of the Sinaloa Cartel, so the whole fire and innocent death lost from it had been all over a drug hit. If Jay had been angry before, he was livid now. He stormed off to the lockers the second the team found out, with Hailey hot on his heels. She found him banging his fist into one and then leaning his head on it in defeat. She approached him tentatively, softly laying a hand on his shoulder and squeezing, letting him feel her presence.

"Hey." She said sympathetically. "Jay, look at me."

He finally looks up again to face her with sad, blanks eyes.

"I really think you need to sit this one out now…" she whispered gingerly, hoping to finally get through to him.

"Hailey, for the hundredth time, I AM FINE! My father did not just save someone's life and lose his own for me to sit back and let some gang wannabe get away with murder."

"Jay-"

"I SAID I'M FINE!" he tells her angerly and pulls her hand from his shoulder.

She stares at him, her patience wearing thin, but the hurt showing on her face that she can't hide from him. He instantly feels remorse, knowing she's just trying to help.

"I'll be okay, really. Look, let's just get the bastard who did this, and then I'll take the time to process everything, I promise." He tells her in a much calmer voice.

She swallows the sigh she has and just nods at him, hoping she won't regret the decision to let him continue on with this case. He squeezes her shoulder this time and they make their way back out to the bullpen.

As the case went on the team discovered that it was Edgar's driver's son, Daniel, a low-level player in the cartel who wanted to make a power move to rise up the ranks; so he killed Edgar and started the fire to cover it up. It was Jay who came up with the idea to bring on a fake charge on Daniel's brother Juan, "the good son" to get the father to flip on Daniel. Not everyone was on board with this, considering it was an innocent man's life at stake, and tensions started to rise even more.

Hailey quickly interjects. "Okay, it's too risky. We get Juan involved, then he's actually involved, the cartel starts gunning for him too!"

"Yeah man, that ain't right! There's gotta be a better way to do this." Adam Ruzek, another team member, agrees.

"Like what?" Jay asks as the team all shares looks. "Exactly, we're at a dead end. I don't even know why we're debating this."

Hailey looks on aghast. She can't believe Jay, who normally shares the same moral compass as her, is even suggesting something like this. She recognizes that this is still affecting him more than he's willing to admit, but she can't agree with what he wants to do.

"Because we're playing with an innocent man's life, Jay!"

"Five other innocent people died because of this guy's not-so-innocent brother and father. So I'm sorry if my heart doesn't bleed like yours!" he responds to her angrily, his frustration boiling over.

Hailey sits up straight now, completely shocked by his direct attack. "Excuse me!?"

As she's about to say more, Voight butts in to break it up. "Okay. That's enough. It's what we have, it's what we'll use. Bring him in."

Jay gives Hailey a pleading look, hoping she'll understand it. He knows he overstepped, but it's not like he can just come out and apologize in front of everyone. He hates that he keeps coming at her especially, but his walls aren't holding up as well as he'd like, and she's the one he's closest to. She's too pissed off herself at this point, so she just looks back at him in disgust and makes her way to the cars.

While Jay, Hailey, and Adam are waiting outside to grab up Juan, Hailey looks at Jay cautiously, fearing how he'll handle this situation. Things escalate once Juan comes out and refuses to go with them willingly. She knows Jay is ready to blow, but trusts him to let it play out. Wrong move. After talking with him didn't go the way Jay wanted it to, he quickly grabs Juan and puts him in a choke hold. While Adam tries to break Juan free of Jay's grasp, it's Hailey who finally halts Jay and pushes him off.

"Jay, back off. BACK OFF!" she screams as she finally breaks through to him. Once Adam has Juan in custody and safely away from Jay, she shoves him again for good measure. She's really angry that she trusted him to stay calm. "You good?" she stares up at him, her eyes fierce.

"Yeah, I'm good." He finally says raising his hands to show defeat. He's terribly irritated with himself now because he knows he keeps setting Hailey off too, but he just doesn't know how to stop himself.

A few hours later they get Daniel's father to call his phone so they can ping his location on the clause that they'll release Juan. Jay heads over to meet Voight with Hailey before the takedown. He has a million ways he wants to apologize in his head, but nothing will come out.

"Hailey…" he starts while quickly looking over at her from the driver's seat.

"Don't Jay, not now. Let's just get through this." She says back to him coolly.

He nods his head at her and before he knows it the car ride is over and they're hopping out to talk with Voight, Jay having no idea this was a setup to keep him away from the remainder of the takedown.

Voight talks over the walkies, "Alright, as soon as we get the location, teams move out. You get there first, you hit it…" once he confirms the rest of his team is good, he turns back to Jay. "Jay… you're not coming!"

Jay turns to look at Hailey first, feeling betrayed. "What?" he asked them both shocked.

"Give her your keys and your two-way." Voight responds in his no-bullshit way.

"You gotta be kidding me." Jay says while replying to Voight, but only looking at Hailey, in complete disbelief.

She looks sad for him, but knows this is in his best interest.

"It's for the best, Jay. Keys and the two-way." Voight reiterates to Hailey again as he starts to walk back to his car.

Hailey finally responds to the situation, trying to be as soft with him as she can. "You're too close to this Jay."

"What the hell does that mean?"

She continues to looks at him sympathetically. "He's your dad…"

"What did you say to him!?" Jay asks her signaling to Voight.

"I didn't say anything!" she replies defensively as they talk over each other.

"You don't know anything about my dad." He responds in anger again.

"I'm not pretending to!" she yells back, her frustrations starting to boil over now as well.

"No, you're just projecting whatever daddy-daughter crap got you screwed up!"

She ignores the low blow and just continues on. "Okay, I'm done being your punching bag. Give me your keys."

He stares down at her and she stares back defiantly.

"GIVE ME YOUR DAMN KEYS!" she yells again, completely over this whole thing at this point.

He shakes his head realizing she's not going to budge from this and hands her his keys.

"Two-way." she responds quickly, not leaving any room for a debate anymore.

He hands it over to her and she swiftly walks to his truck to drive away with Voight, not even bothering to glance in Jay's direction again. He's run her through the ringer these past few days and frankly she's over it. Jay sighs as he watches them drive off, hands on his hips. He knows he's overstepped, especially with Hailey, but he has to see this through. He owes his dad that much. He makes another foolish move and calls Kelly Severide, a local firefighter and friend who offered to help, to pick him up and gain access to his two-way.

Within minutes later Jay has spotted Daniel before his team could and is chasing him on foot down the streets of Chicago. The two come to a standoff while under an overpass, both shooting at and striking the other, falling down to the ground. Jay hears Daniel gurgling out for help as he feels the blood on his side. He can't tell how severe his wound is, but is worried his vest didn't protect him. He knows Daniel is worse for the wear, so he crawls his way over to him, radioing for help. He feels for Daniel's pulse before collapsing on the cold, hard cement. The pain is immense and he knows he's bleeding pretty badly. If this is how it ends, he realizes that his one regret was going to be arguing with Hailey as his last moment with her. She tried to be there for him all week and he continually pushed her away. Leave it to him to screw up one of the few good things that's come into his life the past couple of years.

He starts to hyperventilate, but swears he hears her voice come through his fog. "5021 Henry, officer down, I repeat, officer down, Lower Wacker and Columbus, Get us an ambulance… Jay!"

He feels her soft and warm hands on his chest now as he hears the fear and panic in her voice and Adam yelling in the background.

"Jay, you okay? Come on." She calls out as she tears open his shirt, quickly checking his vest once she does. "It didn't go through; it didn't go through. It's okay." She quickly says as she tries to maintain the shakiness of her voice and hands. "Jay, Jay, breath, breath. You're okay. Okay." He hears her trying to keep him and herself calm.

She puts her hand to his cheek and he leans in slightly, trying to hold back his tears. "Okay." She repeats again, and he's not certain if she's trying to assure herself or him more. She doesn't leave his side until the ambulance arrives, Voight calling her over to finally give her statement to the other officers. She keeps glancing his way though, through Jay's entire checkup and Voight reaming him out, Jay can feel Hailey's eyes on him. Once he's alone again, he sadly watches her walk back over to him. He owes her so much after this week.

He doesn't know how to start, so he just simply asks her about the job. "Daniel?"

She looks at him sorrowfully. "He was pronounced at Med. Antonio's with Juan and Carlos, he's taking them into protective custody. DEA says bodies are already dropping in Mexico, so…"

"So a happy ending?" he asks her and she just smirks at him as they sit quietly for another few seconds.

"Hailey, um… I just couldn't stop myself…"

She nods in understanding, blaming herself for this as much as she blames him, and gently places her hand on his knee to offer comfort. She should have gone to Voight and told him to pull Jay right from the start, but she knew her partner had to see this through. He was as stubborn as she was. Look where it got them though… he could have died. When she thinks back to her and Adam rounding that corner and seeing Jay lying there motionless in a gutter, she tries to choke back tears. Jay notices instantly and places his hand atop hers.

"Hailey, hey, look at me. You okay? I'm so sorry for putting you through this."

She takes a deep breath and wipes away some tears with her other hand. "I thought you were dead…"

Jay looks at her sadly and his heart starts to break knowing he did this to her. It's not often she lets vulnerability show, so he knows she must really be hurting by this. He removes his hand from atop hers, and weary of his injured ribs he slowly puts his arm around her and pulls her into him.

"I'm okay. I'm alright. Won't even need to be put on Light Duty." He whispers in her ear trying to reassure her. "You know how much I would hate that."

She laughs lightly. "Yeah, you would be insufferable!" she jokes back.

They pull away and chuckle together, staring intently, and getting lost in the moment. The tension surrounding them becomes palpable, and they're both drawn to each other in a way they never have before. She watches as Jay's eyes drop to her lips, looking at her in a way that went well past the boundaries of partnership.

"Jay—"

Before she can continue, they're interrupted from their magnetic pull when they hear some commotion coming over by patrol. A woman's voice sounding frantic, finally breaking through the police barrier. It doesn't go unnoticed by Hailey the small groan Jay lets out as his girlfriend, Claire, comes running over to them. The two instantly separating themselves further apart.

"Oh my God honey, Will just called me on my way home from work. I rushed over here. Are you alright? I was so scared!" she says as she touches his face and inspects the rest of his body.

Jay places his hand on hers resting on his cheek. "I'm fine. Just some injured ribs and a potential scar. Plus, a reckless ego that Hailey probably should have killed me herself for, but that's nothing new." He tries to joke to both women.

"Hailey, thank you for saving him. I still can't believe your boss let him work this case. Well, honestly I can't believe how you guys do this job, but I'm just glad you're all okay." She says giving Hailey a hug, surprising the detective.

"Saving his ass is literally what I get paid to do, so it's no worry." She says, trying to make light of the scenario in front of Claire, knowing it's what Jay would want.

She hops down from the ambulance bay and lets Claire take her spot. Jay and her sharing one last look while Claire continues to fawn over him. Jay knows she's about to leave and he wishes he could do anything to get her to stay.

"Hey, you know, Will, Claire, and I were gonna grab some takeout after we look through some of my dad's things. You should join."

Claire nods in agreement, but Hailey would like to be anywhere but around them after the weird moment with her partner just minutes before.

"Thanks, but I'll have to raincheck. Nathan's been texting me all day about when I'd be off and I've barely seen him all week with everything going on, so I should get home. Definitely over the weekend though if you guys need more help. Rest up, partner. Claire, good to see you despite the circumstances."

Hailey replies and quickly starts to turn around before either can respond. She inhales deeply as she feels Jay's eyes burning a hole through her head as she walks away. This far into their partnership she can sense them anywhere… what she doesn't know is how depressingly glum they look as they follow her until she's a small, dark blurb in the distance he can hardly see anymore, but the one thing he wants to hold onto...

* * *

_[A/N: Join me for a journey of another slightly AU Jay and Hailey story. The majority will take place in the time of season 6 of the show, with some flashbacks to 5 and potential future season jumps. Hope you enjoyed this start and thanks so much for reading!]_


	2. Chapter 2

_Hailey and Jay had been partnered for about three months when they caught a case involving an illegal arms deal that turned into a standoff near an unknown, illegitimate daycare center. The team had split up trying to find the suspects whereabouts, when Jay and Hailey stumbled upon them and the men started shooting, then running. Hailey went after the ones who took off inside the building as Jay jumped out of the window after the two who started fleeing outside. Jay was in their direct line of fire, shooting back and managing to kill one of the men. Unfortunately, the other had managed to slip away even though he was wounded by Jay's bullet to his stomach. After Jay moved the body of an innocent bystander, he circled back inside the building to help the rest of the team again. He stumbled upon Hailey and a bunch of screaming children first. Hailey was putting pressure on a gun shot wound of a little girl._

_"What happened?" Jay asks in shock._

_"I don't know, I heard crying!" she explains._

_"Get these kids out the West exit, right now! NOW!" Jay starts yelling to the teachers. "Alright, I'm gonna call an ambulance." He says back to Hailey._

_"We don't have time. Get your car, I'm gonna meet you out front!" Hailey exclaims, picking up the little girl as they run back outside._

_Jay pulls his truck around in record time and helps Hailey get into the back with the little girl. They race to Med as Jay puts out an alert over his walkie for the hospital to be ready, while Hailey continues to try and stop the bleeding. They arrive at the hospital within ten minutes thanks to Jay's heavy foot on the gas, and are met instantly at the emergency entrance by waiting doctors and nurses, including Jay's brother, Will. Hailey and Jay make their way towards the waiting room, letting the doctors do their job. They're too hopped up on adrenaline to sit though. Hailey pacing relentlessly as Jay nervously rubs his neck back and forth. He stops for a moment and notices just how much of the little girl's blood is splashed across Hailey's shirt._

_"Hailey, why don't you go to the restroom and clean up a bit. I'll come grab you if there's an update." He says to her._

_She shakes her head. "No, it's okay. I want to see how she is. Besides, I don't have a spare shirt on me, so I won't be able to clean up much anyway."_

_He nods at her in understanding. Slightly studying her in concern. They pace for a little while longer when they spot Will finally coming out from the curtained room their victim was placed in. They practically jump on the doctor for news._

_"She's in bad shape. But we're doing everything we can!" he tells them._

_"What are the odds?" Hailey asks him._

_"Like I said, we're doing everything we can!" Will reiterates._

_"We know. What about the other two victims, are they okay?" Jay responds._

_"Walk with me." Will tells them as they start making their way down the hall. "James Pell, bullet grazed his leg, he'll be fine we're just finishing up some paperwork."_

_"Hey, what about the other victim?" Jay asks._

_"She didn't make it. Dead on Arrival." Will says solemnly, leading them into James Pell's room._

_Jay and Hailey decide to ask him a few questions, but he claims to not know anything. When they realize he doesn't feel like cooperating they tell him they'll get his contact information and walk away._

_"Come on, we may as well head back to the district and get you cleaned up. Will will update us if there's anything new." Jay places his hand softly on her shoulder and guides her out, happy to see she goes willingly._

_"Yeah. We should find the little girl's mother and inform her." Hailey says as they make their way back to his truck and head out. He nods in agreement._

_They're only at the district long enough for Hailey to change her top and to find out the information on the little girl's family. Her mom, Kamona Williams, works at a local diner and they head straight there. Once they find her, they guide her to where it's private._

_"What's the matter, did something happen?" Kamona asks._

_"It's your daughter, Morgan." Jay tells her._

_"Morgan?" she questions._

_"She was shot, at the old seminary this morning."_

_"No. No." she cries._

_"She's alive." Jay tries to stop her panic._

_"It's okay." Hailey jumps in gently._

_"But is she okay?"_

_"She's being treated at Chicago Med right now. We can give you a ride, okay?" Hailey tells her._

_"Who did this? Who shot her?" Kamona balls._

_"We're not… we're not sure. But we're going to do everything in our power to find him. I promise! Okay?" Jay says._

_"Okay." She nods in understanding, but continues to sob as they guide her out._

_After that moment the hours just get crazier. Morgan was put into a coma because her wounds were so severe. And if that wasn't enough of a blow, ballistics had come back on all the victims. The bullet that had wounded Morgan was from Jay's gun and not one of the suspect's. Apparently, the bullet went through Marcus Kelley, the gang member Jay had shot and who managed to slip away, then went through a piece of wood, then hit Morgan. Jay wasn't handling it well to begin with, how could he, knowing he possibly could cause the death of an innocent little girl? He had witnessed enough unnecessary bloodshed overseas to last a lifetime. But to make matters worse, Denny Woods, a lieutenant who had a beef with Voight was back and now an Independent Auditor for the CPD. He wanted to have Jay's head for this, in huge part due to his hatred towards Voight. But he wasn't their only problem. There was also an Alderman, Ray Price, who wanted justice and vengeance against the police department too. It was in his Ward, it was political, and he was going to see it through. Things were not looking good for Jay. He went back to the hospital for an update on Morgan, keeping at a distance since he probably made the news by now. He makes sure to talk to Will privately down a hall._

_"Her vitals have stabilized a little, she's holding on." Will tells him. "You okay?"_

_"No! Not really, man!" Jay says honestly._

_"Look, I know it's hard to see some punk shoot a lil—"_

_"I shot her! I shot her. The bullet came from my gun."_

_"Your gun?" Will questions._

_"Yeah, so… Tell me she's gonna be okay? She has to make it. I can't have another innocent death on my hands Will, I just can't. Especially a little kid." Jay practically begs his brother._

_"I'm sorry, Jay." Will shakes his head, wishing he could give him better news. "If we can see improvement with her breathing on her own, then we'll start to think about lowering the dosage of meds to gradually wake her from the coma. Full disclosure though, even if she does make it through the worst, the bullet grazed her spine, so there's a chance she may be partially paralyzed."_

_"Jesus!" Jay exclaims, hitting his hands on the wall and then resting his head on it._

_Will's pager goes off, signally he has to go, so he quickly wraps his brother in a hug. It's right at that instant Hailey rounds the corner and sees them, trying to not interrupt their moment._

_"Stay strong, bro. It'll be alright." Will says before walking away._

_"Yeah." Jay nods, disbelievingly._

_Hailey approaches once Will leaves. She calls out for Jay gently. "Hey, I just heard."_

_He shakes his head at her, trying to stop the sympathy, he doesn't need or want it because he doesn't know if he can handle it. He touches her arm and starts to walk away, dismissing the conversation if he can. "I'm okay, thanks."_

_She calls out to stop him. "Jay, look… I didn't see you exchange fire, but I've got your back!"_

_"Just tell the truth. I got nothing to hide." He states, rather coldly._

_"When are you meeting with the shooting team?" she continues._

_"Twenty minutes."_

_"Good luck!" she simply states, giving him the out to walk away._

_"Thanks."_

_Jay walks away, glad to have that over with. Little did he know that his unrelenting partner would be right there waiting for him outside his meeting. He held back a smile, she really was something._

_The next few days after that got gradually better. Morgan started to show signs of being able to breath on her own, so the doctors began to ease her out of her coma. She wasn't out of the woods yet, and it still remained to be seen if she'd be able to walk again, but it was a huge step in the right direction. As for the witch hunt on Jay by Denny and Price, once the team found the original shooter, Marcus Kelley, Denny was left with no choice of fighting it when Internal Affairs wanted to clear Jay of any intentional wrong doing. It was just an unfortunate circumstance. Once that was established, it was very easy for Voight to blackmail Price and get him on his side. Price had no choice but to agree, so he called a press conference to hail Jay as a hero, instead of a villain. Jay was none the wiser on his sudden change of heart, but he was glad to have the public eye part over with. He was still coping with the grief of causing the injury to Morgan, but surprisingly, Hailey had been there for him every step of the way; even when he tried to push her away. He was grateful for his new partner. When the press conference ended, again she was of course the first person he saw. She came running over to him._

_"Hey! Sorry I got here as fast as I could, it's over?"_

_"Yeah it just ended."_

_"How'd it go?"_

_"It was good. Really good actually. Price was very gracious. I'm not really sure what prompted all of this, but…"_

_"Hey, take yes for an answer!.." Jay gives her a small nod back, compelling her to continue. "If there's anything you need, please let me know!"_

_"I'll be okay, eventually, just gotta make sense of all of it."_

_"It's tough, trust me…"_

_"Have you…?"_

_"Yeah, different circumstances, but…" she drags off. "You talk to Morgan's mother yet?"_

_"No, I don't think I'm ready."_

_"Oh man, you're never gonna be ready, you're just gonna have to do it… I can go with you if you want?" she looks up at him, a little unsure, but hopeful._

_"Umm, yeah, that would be great, actually. I haven't really wanted to talk to her alone."_

_"I get it. Come on, my car's around back. You want to stop home and change first?" she asks him._

_"No, I'd rather just get it over with. Finally rip the bandaid."_

_They head to the hospital in silence. Jay lost in his thoughts and Hailey somehow knowing to give him that space. Once they arrive, they see Kamona is in the hospital room with Morgan, watching TV. Morgan looks peaceful and much better than she did, less machines, and breathing on her own, but still unconscious. Will thinks she should be alert again within the next few days. Hailey knocks softly, alerting the woman of their presence; being police officers they were able to get to that point without question. When she hears it, she looks over to them, her expression hard to read. Jay tries to form the words to talk, but nothing will come out. The silence goes on for a bit, almost spurring Hailey to start, but she knows this part is a journey Jay has to do on his own._

_Finally, he whispers out. "May we come in?"_

_Kamona nods her head, but still doesn't speak. Jay shoves his hands in his pockets and looks around nervously. Hailey gently rubs his forearm, trying to encourage him. It gives him the courage he needs. He pulls out a piece of gold jewelry._

_"I found Morgan's necklace at the scene. Thought you guys might want it." He states simply, slowly passing it over to Kamona._

_"Thank you." She says, taking it from his hand, still studying the two detectives._

_Jay swallows. "I also wanted to say how sorry I am. I swear to you, I never meant to hurt your daughter. If I could take that bullet for myself instead, I would."_

_Kamona's quiet for a bit, ignoring his words. "The nurse told me you've come to visit her in secret, always checking in. Thank you."_

_"Of course!" he adamantly replies._

_After another beat of awkward silence, causing Jay and Hailey to share a look, wondering if they should go, Kamona speaks again. "I don't blame you. You couldn't have known these kids were in there. And if it hadn't been for you, and the rest of your team, who knows what would have happened if those thugs caught wind of them. And I know in my heart that Morgan will be okay. So Detective, don't let guilt eat you alive on our account."_

_Jay feels his eyes get wet and swallows to hold back tears, noticing Hailey's eyes are glistening too. He nods back at the young mother in thanks. She has no clue how much meaning her words really hold to him._

_"If it's alright with you, when Morgan wakes up, I'd love to come visit?" Jay asks._

_Kamona smiles for the first time. "I think she'd like that."_

_"Great, thank you. We don't want to take up anymore of your time, but let us know if there's anything you need." He tells her._

_Hailey shakes her head in agreement. "Call us anytime, seriously!"_

_"Thank you, thank you both, especially for rushing her here so fast to save her." Kamona tells them._

_They give her a gentle smile and make their way out. Once they're down the hall a bit, Jay lets out a breath he didn't even realize he had been holding._

_"See? What I tell you? You feel a little better, right?" she smirks teasingly._

_He chuckles. "Yeah, actually. Thank you!"_

_"That's what partners are for, right?" it may sound like a question, but it's definitely a statement coming from her._

_"I guess so." He says and they grin at each other. "Hey, now that I'm not consumed with intense grief, I'm starving. Can't remember the last time I ate. Wanna grab dinner, my treat?"_

_"Sure, that sounds good. If you're in the mood for Italian, Bartoli's has the best dishes and a mean deep dish."_

_"I love Bartoli's!" he states._

_"Really?" she looks at him in excitement. "Everyone laughs at me cause I will choose them over Lou's 90% of the time."_

_"Absolutely. Their pepperoni is to die for." He states._

_"Shutup! Meat Lover's is my favorite from there." She gasps._

_"Upton, I think this is the start of a beautiful partnership!" They smile at each other in happy surprise. It's definitely starting to feel that way…_

_Another few weeks go by and Morgan has shown great improvement. She's fully recovered from the coma, and to everyone's delight has even shown movement in her toes. It will still be a process testing exactly how much motor movement was impaired, but all signs are positive. And the little girl loves when Jay and Hailey come visit. Hailey insisting that first time that she'd go as support for Jay and it just becoming habit after that. Morgan is just as feisty as Hailey, so the two have a blast together making fun of Jay. He feigns hurt, but secretly he enjoys every minute of it. The little girl has warmed his heart, and he'd be lying if he didn't say his partner did too. Hailey's been such a rock for him, and it's not something he's used to. He's never been able to count on someone the way he can her. He's thankful every day that they stumbled on a Robbery-Homicide case she was working, and then pawned her to Intelligence. She was by far the best partner he's ever had, even in just a few months, and she slowly started to become a good friend too. He can't picture his life without her in it every day anymore._

_They're leaving from one of their many visits and now in the parking lot making their way back to his truck. He's just about to ask her if she wants to grab some food or a drink, when her phone starts to ring. It had been going off in the hospital, but he noticed she was trying to ignore it. She always tries to give Morgan her full attention, so he didn't think much of it at the time. Now he sees her finally answer. They're standing at the truck now and he doesn't want to listen, but he isn't sure if it would be rude to just get in the truck while she's standing outside. So he fidgets with his keys, trying not to seem completely noisy. He hears her name the caller Nathan. She seems to apologize a few times, then assuring him she would make it in time for dinner tonight, ending with a "love you too." He swallows hard, realizing the context and not sure how he feels about it. She hangs up and notices him watching her, getting apologetic instantly._

_"Sorry for that… just, I had promised my boyfriend we'd actually go out for dinner tonight since our schedules aligned, but I forgot how long some of our Morgan visits could be."_

_"You have a boyfriend? How did I not know this? We've known each other since spring." Jay asks shocked._

_Hailey chuckles awkwardly. "Yeah, sorry. I just don't usually talk about my personal life. His name is Nathan, we've been together about two years now. He's a lawyer so both of our schedules are kind of everywhere."_

_"Wow, a lawyer, huh?" he teases her impressed._

_"Yeah, I actually majored in Law for a minute. My parents, especially my dad had really wanted me to become one. Maybe subconsciously Nathan appeases that."_

_"Huh! The more I learn about you Upton… well, don't let me keep you any longer. Let's get you back so you can get ready." He smiles at her softly, trying to ignore the tightness in his chest._

_"Thanks, Jay." She smiles back, not only thanking him for trying to help her time schedule, but for understanding and not questioning too much. Understanding that she needs that space still and understanding that she didn't tell him about Nathan, when they spend 13 hours a day together. She's not entirely sure why she didn't tell Jay. She's also not entirely sure she wants to question the why of that too much right now. They stare back at each other, and somehow, they both get all of that with just one look. It's just this eerie connection they have. They hop in the truck and don't speak anymore until they're back at the district, in the lot next to Hailey's car._

_"Thank you." She says again._

_"Anytime, Hailey!" they smile and she gets down from truck when he speaks again "…and for the record, Hailey, Nathan's a lucky guy!"_

_They stare at each other once more, it's a distant car horn that breaks them from their spell. Yup, an eerie connection that can't be explored…_

_Hailey sticks with what's safe. "Have a good night, Jay!"_

_"You too, Hailey."_

_He quietly says back. He should be happy his partner is happy with someone. And he convinces his brain he is. But his heart can't seem to escape the feeling of sadness of losing something he never had in the first place…_

* * *

[Hope you enjoyed this flashback to 5x01 times. A little back story to the development of their partnership/friendship. In this mildly AU story Upzek clearly doesn't exist, Linstead wasn't a thing, Morgan survives- so no insanely spiraling Jay, and two OC's who won't be prominent. Hope you're ready for the ride. Thank you so much for all of your kind reviews so far and for reading. Stay safe!]


	3. Chapter 3

It had been a few months since Jay's dad had passed away and Jay got himself shot trying to avenge his life. Despite all that, things had been going relatively well since. He was able to find some closure looking through his father's belongings and his friendship with Hailey and the rest of the team had been a saving grace. Things with Claire had even been going okay, despite the better half of their relationship being on rocky ground. She was a great girl, it was just that she hated his job, which was understandable, but maybe it made him a bit more irritable because there was always someone else on his mind… Someone who _did_ understand the job and him and always had… but she wasn't in the cards romantically, so he had kept trying to make it work with Claire. It had seemed the façade of acting fully happy was working.

For once, Jay had thought things had started to look up until they caught a case of an Alderman's wife being beaten to death in their home. A local kid, Devin Williams, a recurring junkie, had looked good for the murder. He fit the description of witnesses and he had run from the police when confronted. They just needed a confession and they could wrap it up. Hailey had actually been the one who got him to open up to her. She played to his abusive past, telling him it wasn't his fault, and in turn got a confession out of him. Unfortunately, with his mental state it turned out to be a false confession. By the time they had put two and two together, that Devin was high in the park far away from the house like he originally stated, it was too late. When Hailey and Trudy Platt, their Patrol Sergeant, went to his holding cell to question why he falsely confessed, Devin had killed himself moments prior. Hailey was completely distraught. When the two women returned back to the bullpen with the news, Jay immediately saw the tears in her eyes and wrapped her up in a hug. Voight gave them both the rest of the night off and Jay took her home. Which is how they found themselves drinking around her kitchen island for what now felt like the 100th time after a rough case or personal dilemmas. Jay waited patiently as Hailey laid with her head in her hands staring at her tequila. It was starting to hit him that he'd quite literally wait a lifetime for her, in more ways than one.

"He was telling the truth. Kid was a Humboldt Park the whole time." She finally looked up and started letting it out. "I was so desperate to get a confession, I didn't even consider the fact that he could be innocent. I just kept poking at his pain… his wounds…" tears slowly filled her eyes again.

Jay moved closer to her, sitting right next to her so she knew there was no question he was in her corner. "Hailey, you did what you were supposed to do." He tells her as she slowly sips her drink. "You had a suspect in the box without a lawyer, you got him talking, and you exploited a weakness."

"I exploited a 20-year-old kid's tragic past…"

"All the evidence pointed to Devin. I would have done the same thing."

She sighs and runs her hand over her forehead and hair. "I know… I just can't get seeing him out of my head. He was just lying there, lifeless, hanging from his cot post when Trudy and I arrived. I kept trying CPR and she had to pull me away. It was only a couple hours before he was a full of life well-mannered kid, talking gibberish off his high and just wanting a pop. I brought back memories that I of all people should know are buried down deep for a reason. Reasons they should stay buried if you're not in an appropriate state to handle them."

Jay reaches his hand out to her wrist in a gesture of comfort. "Hailey, there was no way you could have known what he would do. Maybe he falsely confessed because he knew it would be his out… you're a good person. The best person I know. You can't beat yourself up over this. Sometimes this job gives us a really shitty hand to deal."

She does her best to give him a small smile, to reassure him she appreciates it. "Thanks Jay, I just think I'm gonna need some time with this one. It hits a little too close to home and I should have known better. I'll be okay though, especially once we catch the real killer. Devin at least deserves that from us."

"We'll get him. Listen Hailey, about…" before Jay can finish, they hear the key in Hailey's front door and the creak of it opening.

They both instantly separate themselves a bit, as if they feel guilty. Which is silly because it's just two partners comforting each other after a hard day at work. Clearly, subconsciously, they both realize that maybe it's a little bit more than that. Jay sits up straight in his chair and Hailey wipes the tears from her eyes and puts on a fake smile just as Nathan walks into the kitchen.

"Oh, hey Jay, how's it going? I thought I saw your truck out front." Nathan says.

"Hey hun." Hailey continues her fake smile.

"Good man, thanks. How are things with you?" Jay replies.

"Busy, it always seems like the closer it gets to Fall ending and the holiday season coming, the more people want to file lawsuits. So jolly. But I can't complain." Nathan jokes.

"Ha, I'll bet." Jay says, playing cautious, knowing Hailey is being oddly quiet.

Nathan looks at the bottle and their glasses on the table. "Ut oh, tequila, huh? That bad?"

"Just a rough case, nothing major." Hailey quickly said and smiled at her boyfriend.

When she caught Jay giving her an odd look, she silently begged him with her eyes to leave it be. Jay caught on, it clear that she wasn't going to tell Nathan tonight what had happened, if ever. Jay silently swallowed his thoughts and played along. It wasn't his place to say anything if Hailey didn't want him to know.

"I have some of that leftover pizza I can heat up if you guys want?" Hailey continues.

"That sounds great." Nathan says as he walks over to give her head a kiss and then grabs a beer out of the fridge. "Jay, you wanna catch the end of the game? Last I heard on the radio Hawks were up 3-2."

Jay hesitated for a moment, but then replied, "Sure." He started to follow Nathan to the living room, but gave Hailey's shoulder a squeeze as she turned on the oven to preheat. She gave him a small smile in thanks and he knew she'd come in with them shortly.

Jay stayed until the end of the game before leaving. Over the past year and a half that he knew Hailey, he had also hung out with Nathan a bunch of times too. They even did a guy's night once. He had really wanted to hate him, but he was actually a pretty standup guy, even for a lawyer. He was funny, Jay got along with him, and he treated Hailey well. Sometimes the guilt would eat Jay up inside because he was harboring deep buried (although rising to the surface more and more) feelings for his girl. Feelings that he had managed to keep at bay since he had met Claire to distract him from the truth, but that could only work for so long. Tonight had been eye-opening for Jay, knowing Hailey was so distraught and wanting to be there for her the whole night, but it not being his place. It killed him even more to know she wasn't even going to open up to her own boyfriend like she does with him. She kept up the happy persona the rest of the night, but Jay saw right through it. She looked so sad when he said goodbye, he so wished it was him who was staying the night with her. He couldn't do this anymore. Maybe he couldn't be with the one he wanted, but he couldn't continue to live a full lie. It wasn't fair to anyone. He knew what he had to do.

* * *

By the time he pulled up to Claire's condo it was almost eleven. He's sure she's probably not happy about it, but to her credit she tries to understand. She deserves more than him. Someone who would truly put her first. She had given him a key a couple months ago, which he felt was maybe too big of a step, but he let it be. He wasn't comfortable using it often, but since he texted her on his way over, he helped himself inside. He found her watching television in the living room in her pajamas. Her favorite tea cup in hand. She gives him a smile, but he can tell it's not reaching her eyes. In an odd way it reminds him of how Hailey looks at Nathan, or maybe that's just wishful thinking on his part.

"Another late-night long case?" she asks as he comes to sit down next to her.

"Something like that." He replies and she just nods.

"So what brings you by? I figured you were staying at your place tonight when I didn't hear from you."

He sighs deeply, always hating these types of conversations. "I wanted to talk, actually."

She looks at him and mutes the television, as if she already knows what's coming.

"Claire, you know I really like you. You're a great girl, beautiful, smart, the whole nine. But we both know that you hate that I'm a cop…"

She cuts him off. "Jay, if we're going to do this, can you at least be honest with me? I deserve that at least."

For a moment he's stunned. "What do you mean?"

"It's Hailey, isn't it?"

"What? There's nothing going on between me and Hailey! I swear to you!"

"Maybe not, but you want there to be. Come on, Jay, I'm not stupid… it's always been her. Even the night we met you couldn't stop talking about your ' _partner_ '" she air quotes.

Jay tries to think back, has it always been that obvious?...

* * *

_Jay was sitting in Molly's after a hell of a few weeks. It was only an hour prior that Hailey had dropped him off at his apartment after they had gone for a drink at a local dive bar. Once he had gone inside and sat for a few minutes, he just felt he had to get back out and ordered an Uber to take him to Molly's. It was a pretty quiet night there, with only a few people he knew around, which he was thankful for. He wasn't drunk, but he definitely had a good buzz going on, and he was looking to enhance that, but not in the depression of his own apartment. He felt like the demons could return if he stayed there by himself. But he couldn't tell Hailey that, because then she wouldn't leave him alone, and he had already taken up enough of her time this past month. She deserved to get home to her boyfriend, even if there was a small part of him that secretly hated it._

_She kept proving how loyal she was to him and how much she'd go to bat for him. He can't remember the last time he had someone like that. Maybe some of his army buddies? But even them, they had their own demons to deal with, those who survived, so he got it. Even the rest of Intelligence, he'd been with them all for five years now, but no one quite had his back like Hailey had in just eight months, and only partnered through six of them. He tested it the most this month when he had gone under for a K &R gang that had army ties. His alias had befriended Luis Vega, one of the players in the group who was a veteran who served at the same time as him. Having to go under like that, it had drudged up a lot of bad memories he had tried to keep buried. On top of that, he had to develop a flirtation with Camilla Vega, Luis' sister in hopes to get him to let his guard down. It had worked, but one thing had spiraled into another, which spiraled into another. Luis agreed to help Jay to take down his boss, but he got caught in the crossfires and he got killed in the standoff. That had really triggered Jay's PTSD a little and he went to comfort Camilla (and maybe himself) and ended up sleeping with her. He felt horrible about it, using her, lying to her, guilt over lying to Hailey and the rest of the team. But he figured all would be okay if it was a one-time deal, which he kept it to even though Camilla wanted more. Unfortunately, it spiraled again when it turned out Camilla had been heavy into drug dealing and an undercover DEA agent who had been investigating her ended up dead. The rest was a nightmare, he had to come clean to Hailey in case Camilla found a way to implicate him. Hailey was livid, but somehow, she found a way to make it disappear for him, even if he didn't deserve it. She made him promise her he would go to therapy and that he'd never do something so stupid again. He swore he wouldn't. Even after putting her, and the team, all through that, she still took him out for a drink tonight and stood by his side. The wounds and his stupidity were fresh, but she proved to him there was nothing he couldn't get through as long as he had his partner. He vowed to himself to be the man she deserved… at work, of course._

_So what if he was feeling a little depressed that she was going to spend the rest of the night with her boyfriend. It had just been a long few weeks and he was feeling sorry for himself, that's all it was. It didn't matter that he saw that certain blonde every time he closed his eyes. It's just what happens when you spend so much time with someone every day… at least that was the lie he was telling himself again as he chugged down the rest of his whiskey._

_"I'll have what he's having!" said a female voice to his left._

_He turned and realized a pretty brunette had sat right next to him. Stella Kidd, the bartender tonight, and one of the firefighter's over at Station 51, started laughing._

_"Are you sure? Halstead here would drink off the bar mat if the occasion called for it!" Stella joked to the brunette._

_"Hey, that was one time!" Jay cracked back, trying to get in the spirit. It was better than sitting there depressed thinking of someone off-limits._

_"Well, I don't know about all that, but if his last drink was a whiskey neat, I'm in." the girl chuckled as she told Stella._

_"Coming right up. Jay, another?"_

_He nodded to Stella._

_"Sorry to interrupt, but you looked to really enjoy pounding down that last bit, and I just got off work so I could use one."_

_"Happy to share the bar. I'm Jay." He said as he reached his hand out to shake hers._

_"Claire." She smiled at him._

_"So tell me, Claire, what line of work brings you to a bar at—" he stops to dramatically look at his watch, "10pm on a Wednesday?"_

_"I'm an art curator. The exhibit I setup ran longer than intended." She shrugs as Stella comes over with their whiskeys._

_"An art curator, huh? I don't come across many of those, but I imagine Chicago has a lot of work for that."_

_"Yeah, we're definitely not a common job title, but I enjoy it… usually. Chicago has been great. I'm from New York originally, so there was definitely a higher grind and a bigger art world there, but I was looking for a change." He smiles at her since she seems nice enough and she takes a sip of the drink and breathes in. "Ooh, I don't drink whiskey plain very often, sorry. I'm more of a tequila girl."_

_He grins and before he even realizes it, the words slip out of his mouth. "Yeah, Hailey is too."_

_Claire gives him a knowing, slightly disappointed look. "So you have a girlfriend?"_

_He's taken back and confused and it takes him a moment to realize he had said that aloud. "Oh who, Hailey? She's my partner."_

_"Is that your term for a committed relationship, but not marriage yet?" She teases him._

_"What? Oh, no, sorry. I mean she's my work partner. We're detectives."_

_"Wow, I'm in the presence of CPD? That's intense!"_

_"It definitely has its moments… so it's good to have a partner you can rely on…"_

* * *

Jay remembers that night close to a year ago now and he can't believe how naïve he's been. He does remember talking about Hailey a lot that night, and if he's being honest, a lot throughout his relationship with Claire. But she had never really questioned it… maybe because she always knew. Maybe they were both using this relationship to suit their own needs. Him to distract from his feelings for Hailey, her to not be all alone in a new city hundreds of miles from home. He had gotten Claire's number that night and they had gone out that weekend, slept together and everything, they just kind of fell into it all.

"Claire, I'm so sorry…" he tries.

"Jay, don't be, it's okay. We had a great run. Did I hope that one day maybe you could feel for me what you felt for her? Of course. But we can't help who we love…"

"I don't…" he swallows, knowing not only can't he lie to her anymore, but himself also.

"You know Jay, for an elite detective, you're pretty aloof." She teases him and he grins a little, relieved how well this is going all things considered.

"I hope it works out for you, Jay. I have a feeling it's not one-sided."

"I don't know about that, but thank you for being so understanding. You're really a great catch for a Yankees fan." He smiles at her as he pulls her into a hug and kisses her forehead. "Please take care of yourself, okay?"

"You'll be my first phone call if I ever need police assistance." She winks at him as they make their way to her front door.

He gives her one last hug and whispers a "thank you" in her ear. When he gets back to his truck he lets out a sigh of relief. He knows she'll find someone amazing, it just was never going to be him. That night he sleeps well for the first time in a while, a huge weight lifted of the feelings he was trying to hide. He may just be Hailey's partner and friend, but he wouldn't run from his feelings anymore. If anything, he'd embrace them and show her just how good of a friend he could be. She clearly opened up to him more than anyone else, and he would continue to be that shoulder she could lean on.

The next morning when he picked her up he had her favorite coffee waiting and gave her a sweet and patient smile as she got in the car.

"I know you don't wanna talk about it… but I wanna make sure you're okay." he told her softly before driving away.

She smiled brightly, her blue eyes twinkling, at his words and at the coffee he was handing her and somehow, he just knew things would work out as they were meant to…

* * *

_[A/N: Thank you for all your kind words and reading thus far, appreciate it. Little odes to 6x06 and 5x10 in this chapter. So one significant other storyline swiped away... can we eventually make it two? ;) Or is Upstead not meant to be? ooooh the suspense, haha! Until next time! Take care xoxo]_


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